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From behind bars, Juan Guzman ran a multimillion-dollar drug ring with the help of his sister, a state employee, providing cocaine from Mexico to the streets of Boston, according to authorities. On Monday, their enterprise was brought to an end by the largest drug ­investigation in the city in at least a decade.

Fourteen people were arrested just after dawn by about 100 Boston police officers and FBI agents in 12 locations across Boston, Milton, and Canton, dismantling an illegal operation that authorities likened to the television show “The Wire.”

Through the morning and early afternoon, authorities seized about $500,000 from 12 residences, four vehicles, nine bank accounts, and a safety ­deposit box allegedly used by the drug ring. The amount of cocaine seized was still being tallied Monday night.

“Today’s arrest and seizures amounted to a corporate takedown,” said Suffolk County District Attorney Daniel F. Conley, who announced the arrests at a press conference. “The managing partners are behind bars, and their product is out of circulation.”

Authorities described the so-called Guzman Trafficking ­Organization as highly organized and violent, with close ties to the Boylston Street gang, which they said has been respon­sible for violence in ­Jamaica Plain, including a triple homicide in 2010.

“If you imagine a pyramid with narcotics manufacturers at the very top and street-level users at the very bottom,” ­Conley said, “the Guzman Drug Trafficking Organization — with its wholesalers, distributors, and financial managers — would be within the top third.”

Guzman, 33, directed operations while serving a 2½-year sentence at the Massachusetts Correctional Institution at ­Concord after a 2011 conviction on gun and drug charges, Conley said. Authorities said they monitored “dozens and dozens” of Guzman’s conversations while he was behind bars.

“Those of you who watched the TV show ‘The Wire’ will ­recall the Barksdale Crew, whose leader was incarcerated throughout the second season, and you wouldn’t be far from the mark,” Conley said. ­Guzman, he said, was “aided and enabled by an inner circle of top-level distributors and confidantes.”

Guzman’s sister — Maria ­Guzman, 28 — worked as a secretary at the Dorchester Juvenile Court, and is accused of maintaining bank accounts and a safety deposit box containing drug proceeds, authorities said. The deposit box and her accounts were seized, as were the accounts of Martha Tejeda, 54, the mother of Guzman’s fiancee, and Tomas Soto, 34. Guzman, ­Tejeda, and Soto were arrested Tuesday.

Three additional accounts and a Mercedes sport utility ­vehicle were seized from ­Melissa Mejia, 28, described as Guzman’s fiancee. Mejia, who was also arrested, managed Guzman’s personal finances during his incarceration, accord­ing to authorities.

The group had large amounts of cash on hand, and posted bails as high as $50,000 when associates were detained, authorities said.

Also arrested was Rafael Vasquez, 28, who is accused of being Guzman’s primary distributor and day-to-day head of operations, according to the district attorney’s office.

“This is a very organized, ­sophisticated narcotics distribution network that engages in violence that has been taken out today,” Boston’s police commissioner, Edward Davis, said after the arrests.

Several alleged members of the ring are also members of the Boylston Street gang, said Conley, an especially violent and brazen group whose clashes with a rival Jamaica Plain group, the Mozart Street gang, are linked to at least seven ­homicides over the last five years, and the shooting of a 6-month-old in 2008. The infant’s liver was pierced by a bullet as her father cradled her in his arms.

A 2010 triple-homicide at a Centre Street pizzeria — a fistfight that escalated into a shooting — is also believed to be connected to the rivalry. “This is a group that regularly used violence to achieve its ends,” Conley said.

A law enforcement official with knowledge of the gangs said the rivalry dates to at least 2007, when members of both groups saw each other at a Rhode Island nightclub and started fighting. The groups have had bad blood ever since, but the rivalry is not believed to be rooted in drugs, the official said.

After the pizzeria shooting, violence between the Boylston and Mozart gangs has ebbed over the last two years.

“We are holding people account­able for the violent ­activity they are responsible for,” Davis said.

The 13-month investigation into the trafficking included thousands of hours of physical surveillance, forensic accounting, translation services, GPS tracking, confidential sources, and a “tremendous” amount of electronic surveillance, Conley said. Prosecutors went to court nine times to obtain wiretaps on at least 12 phones used by Guzman associates.

“It was a criminal syndicate akin to the Mafia,” Conley said. “When you get an elaborate organization like this, that’s very secretive and sophisticated, ­ordinary law enforcement cannot infiltrate.”

About 2½ weeks ago, a car stop yielded 10 kilograms of ­cocaine, a small amount for the Guzman organization, which officials said distributed hundreds of kilograms of cocaine per year, and received individual shipments of up to 40 kilograms. The cocaine is believed to have come from Mexico.

The federal Organized Crime Drug Enforcement Task Force, formed to combat drug activity in and around Boston, was used to take down the ­Guzman organization, said Richard DesLauriers, special agent in charge of the FBI’s ­Boston division.

The task force includes agents from the Drug Enforcement Administration; Bureau of Alcohol, Tobacco, and Firearms; Department of Homeland Security; Internal Revenue Service; and the Boston Police Department.

Twelve people face charges of conspiracy to traffic in more than 200 grams of cocaine, a felony punishable by up to 10 years in state prison and/or a fine of up to $10,000. Three of them could also face laundering charges, Conley said.

At their arraignments Monday, bails were set for between $10,000 and $25,000 for four defendants; prosecutors had asked for $100,000 cash bail. Attorneys for those defendants could not be reached Monday night.

Guzman was not arraigned Monday, but will be brought to court later, the district attorney’s office saud. The others are to be arraigned Tuesday.